Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/08—Anti-ageing preparations

Definitions

• the present invention relates to substances which can be used as cosmetic ingredients, especially for skin whitening and as cosmetic agents against signs of ageing skin.
• the present invention also relates to the use of such substances for the manufacture of a medicament for the treatment of disorders related to the pigmentation of the skin.
• 2-(4-Hydroxyphenoxy)alkanoic acids are known as intermediates for herbicides or dyes, e.g. described in EP0334595.
• One object of the invention was to provide substances which can be effectively used for the manufacture of or in cosmetic compositions and which are especially suitable as skin whitener and/or as cosmetic agents against the signs of skin ageing.
• Of special interest was to provide substances which are chemically stable and can thus be easily incorporated into cosmetic compositions.
• these substances do not, or only to a much lower extendt than products known in the market, cause an irritation of the skin onto which it is applied.
• a further aim of the invention was to provide substances for the manufacture of a medicament for the treatment of disorders related to the pigmentation of the skin.
• the present invention relates to the use of at least one substance of formula (I)
• the substances according to formula (I) comprise an optically active C atom.
• Suitable according to the invention are substances according to formula (I)
• Y is selected from the group consisting of H, an alkyl or alkenyl group comprising 1 to 8 carbon atoms, a phenyl group, Na + , K + and NH 4 + .
• Y is selected from the group consisting of H, and an alkyl or alkenyl group comprising 1 to 8 carbon atoms.
• the alkyl or alkenyl groups can be linear or branched.
• Y is selected from the group consisting of H, an alkyl or alkenyl group comprising 1 to 3 carbon atoms, Na + and K + .
• Y is H.
• R 1 is —H, a linear or branched, saturated or unsaturated alkyl group comprising 1 to 18 carbon atoms, —C( ⁇ O)—R 2 , wherein R 2 is a linear or branched, saturated or unsaturated alkyl group comprising 1 to 17 carbon atoms or —(CH 2 ) n —COOX wherein n is 0 to 17 and wherein X is H, an alkyl or alkenyl group comprising 1 to 8 carbon atoms, a phenyl group, Na + , K + or NH 4 + ,
• R 1 is —(CH 2 ) n —COOX wherein n is 0 to 17 and wherein X is H, an alkyl or alkenyl group comprising 1 to 8 carbon atoms, a phenyl group, Na + , K + or NH 4 + .
• R 1 is —(CH 2 ) n —COOX wherein n is 0 to 17 and wherein X is H.
• R 1 is —H, a linear or branched, saturated alkyl group comprising 1 to 12 carbon atoms, preferably 1 to 3 carbon atoms.
• R 1 is —(CH 2 ) n —COOX wherein n is 0, 1 or 2 and X is H.
• R 1 is —CH 3 and Y is —H.
• R 1 is —H and Y is —H.
• the substances according to formula (I) are either commercially available, such as for example 2-(4-hydroxyphenoxy)-propionic acid [CAS N o 67648-61-7], (R)-(+)-2-(4-hydroxyphenoxy)-propionic acid [CAS N o 94050-90-5] or (4-hydroxyphenoxy)-acetic acid [CAS1878-84-8], all from Sigma-Aldrich, or can be obtained by known methods of preparative organic chemistry, or by microbial or enzymatic hydroxylation of related phenoxy-compounds.
• Cosmetic compositions shall mean any preparation intended to be placed in contact with the various external parts of the human body (epidermis, hair system, nails, lips and external genital organs) or with the teeth and the mucous membranes of the oral cavity with a view exclusively or mainly to cleaning them, perfuming them, changing their appearance and/or correcting body odours and/or protecting them or keeping them in good condition.
• the cosmetic compositions according to the invention can for example be in the form of a hair shampoos, hair lotions, foam baths, shower baths, creams, gels, lotions, alcoholic and aqueous/alcoholic solutions, emulsions, wax/fat masses, stick preparations, powders or ointments.
• compositions can also comprise, as further auxiliaries and additives, mild surfactants, oil bodies, emulsifiers, pearlescent waxes, consistency regulators, thickeners, superfatting agents, stabilizers, polymers, silicone compounds, fats, waxes, lecithins, phospholipids, UV photoprotective factors, biogenic active ingredients, antioxidants, deodorants, antiperspirants, antidandruff agents, film formers, swelling agents, insect repellents, self-tanning agents, hydrotropes, solubilizers, preservatives, perfume oils, dyes and the like.
• the substance according to formula (I) can be used in cosmetic and/or topical compositions in an amount of 0,0001 to 10 weight-% based on the total weight of the composition, preferably in an amount of 0,001 to 5, especially in an amount of 0,01 to 3 weight-% based on the total weight of the composition.
• the present invention also relates to cosmetic and/or topical compositions comprising a substance according to formula (I) and at least one skin-whitening active.
• compositions of the present invention comprise at least one substance according to formula (I) [preferably as a skin-whitener] and at least one (other) skin-whitening active, which is different from a substance according to formula (I).
• the two actives can act synergistically to provide a highly efficient cosmetic composition.
• the further skin-whitening active can be chosen from any known skin-whitening agent, e.g. kojic acid, hydroquinone, alpha- and beta-arbutin, other hydroquinone glycosides, deoxyarbutin, ferulic acid, diacetyl-boldine, azelaic acid, octadecenedioic acid, linoleic acid, conjugated linoleic acid, alpha-lipoic acid, glutathione and derivatives, undecylenoyl-phenylalanine, vitamin C and derivatives as magnesium L-ascorbyl-phosphate, niacinamide, 4-n-butyl-resorcinol, alpha- and beta-hydroxy acids, ellagic acid, resveratrol, Morus alba extracts, glabridin and liquorice extracts, imperatorin and isoimperatorin and Angelica dahurica extracts, centaureidin and Yarrow extracts, Bellis
• the further skin-whitening active is at least one plant extract.
• the further skin-whitening active is selected from the group consisting of kojic acid, alpha- and beta-arbutin, other hydroquinone glycosides, deoxyarbutin, ferulic acid, conjugated linoleic acid, vitamin C and derivatives such as magnesium L-ascorbylphosphate, niacinamide, liquorice extracts and combinations thereof.
• compositions are especially suitably used for the lightening and/or whitening of skin and/or for the reduction of pigmentation and/or reduction of hyperpigmentation and/or inhibition of melanogenesis.
• the invention encompasses the finding that substances of formula (I) as well as the compositions are especially suitably used for the prevention and/or retardation of signs of ageing and/or improving the skin appearance of aged skin, such as for example sallowness, decrease of skin thickness, fine lines, wrinkles, sagging, diminished rate of turnover, abnormal desquamation.
• the invention is further directed to the use of a substance according to formula (I) for the manufacture of a medicament for the treatment of a disease connected to a disorder in the pigmentation of the skin.
• hyperpigmentation diseases are for example chloasma (a hypersecretion of melanin induced by hormonal factors and amplified by the effects of sun exposition), lentigines, solar and senile lentigo, Dubreuilh melanosis, or any form of hypermelanosis or melanocyte dysfunction.
• FCS foetal calf serum

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Dermatology (AREA)
• Emergency Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Gerontology & Geriatric Medicine (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Engineering & Computer Science (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Medicinal Chemistry (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Organic Chemistry (AREA)
• Pharmacology & Pharmacy (AREA)
• Toxicology (AREA)
• Cosmetics (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (4)

Publications (2)

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Citations (4)

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• 2007
  • 2007-03-06 EP EP07004524A patent/EP1967176A1/en not_active Withdrawn
• 2008
  • 2008-02-26 KR KR1020097018424A patent/KR101517630B1/ko active Active
  • 2008-02-26 EP EP08716033.9A patent/EP2117498B1/en active Active
  • 2008-02-26 WO PCT/EP2008/001491 patent/WO2008107092A2/en active Application Filing
  • 2008-02-26 US US12/530,342 patent/US8247447B2/en active Active
  • 2008-02-26 ES ES08716033T patent/ES2436289T3/es active Active
  • 2008-02-26 JP JP2009552095A patent/JP5479113B2/ja not_active Expired - Fee Related

Patent Citations (4)

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